Chloroacetyl chloride → 5,6-Difluoro-4H-benzo[1,4]oxazin-3-one

Participants

Reaction Steps

A crude of 2-amino-3,4-diflourophenol (0.68 g, 4.7 mmol), 2-chloroacetyl chloride (0.58 g, 5.2 mmol) and K2CO3 (1.36 g, 9.9 mmol) were mixed according to GP1. Purified by prep RP-HPLC to give the title compound (0.127 g, 14.5%). Rf=0.63 (heptanes/EtOAc 1:1). 1H NMR (CDCl3) d 6.69-6.57 (m, 2H), 4.47 (s, 2H); 13C NMR (CDCl3) d 165.0, 146.2 (dd, J=241.8 Hz, J=10.4 Hz), 140.3 (t, J=2.32 Hz), 138.7 (dd, J=247.2 Hz, J=17.3 Hz), 67.1 (t, J=2.7 Hz).

Provenance & Evidence